Abstract
A novel two-step method for the preparation of 6-deoxychitin from N-acetylchitosan (1) is described. Compound 1 was prepared by N-acetylation of chitosan, and was specifically brominated at C6 to afford 6-bromo-6-deoxychitin (2). Compound 2 was treated with NaBH4 in dimethylsufoxide to give 6-deoxychitin (3). Repeated treatment of 3 with aq 40% NaOH at 100 °C for 10 h gave 6-deoxychitosan (4). Compound 3 was insoluble in aq 2% acetic acid, but 4 was soluble in aq 2% acetic acid. Compound 3 was hydrolyzed by chitinase from Bacillus sp. at a rate of 0.8 time that of 1. 1. Presented at the XVIII International Carbohydrate Symposium, Milan, Italy, July 21-26, 1996.
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